Vampire Pirates
by Isadogger
Summary: Mystic Fall's teens get more than they bargained for when stealing a boat results in them getting kidnapped by vampire pirates terrorizing the seas on their dreaded ship, the 'Salvatore'. !dark AU, Disclaimer: I don't own the show or characters in this story.
1. Meet The Pirates

Author's Note:

Warning: !dark OOC AU, likely non-graphic non-con in later chapters (um...evil pirate vampires duh)

Non-canon AU, None of the pirates are werewolves or 'originals' or hybrids, they're just vampires, although most of them are at least a few hundred years old and were born in the 1600's and turned during the Golden Age of Piracy between the 1650-1720's, but this story isn't likely to worry about dates. Also, Stefan doesn't have any humanity and may not ever.

Probable pairings: Bamon, Rebenzo, Klaroline, !darkStelena

Pirates on board the _Salvatore_ : Captain Damon Black, First Mate Enzo Longjohn, Bosun Alaric Saltydog, Stefan Ripclaw, Saint Niklaus, Kol Slawter, Mason Lockbeard, Mad Malakai, Mikey Mikaelson, Billyboy Forbes, Logan Scumfell

* * *

Meet The Pirates

* * *

"Yo, ho, ho, and a bottle of bourbon!" Bosun Alaric Saltydog sang out drunkenly as he carelessly kicked over a poorly placed bucket of water that one of the human slaves was using to scrub the deck. The suds splashed over the boots of Stefan Ripclaw who spun around with an evil sneer at the human cowering in fear.

"Well, aren't you a pathetic little klutz," he said, glaring at the man who was trembling so much he failed to set the bucket upright and it rolled over to Stefan's feet. "What are you waiting for blood bag? Pick up the bucket."

The human reluctantly inched forward and reached for the bucket, as the pirate standing over him slashed down with his hook, piercing through the human's hand as his fingers wrapped around the bucket handle.

"Let me lend you a hand." Ripclaw laughed at the screaming man, pulling him up to his feet and tearing the left handed hook out, watching as the bucket fell back down to the deck and the human backed away clutching his bleeding appendage.

"Seriously, you dropped the bucket _again_." Stefan's eyes began to writhe with the dark vampire veins as he licked the blood from his hook and advanced on the helpless slave.

"Ripper's gonna rip!" shouted Kol Slawter playfully from the ropes above while setting the sails.

A handful of bloodthirsty pirates gathered their eyes on Ripclaw's menacing advance towards the cowering slave, beginning the chant, "Ripper, ripper, ripper, ripper!"

Suddenly, a dark shadow cast down from above them as the captain's voice rang out, "STEFAN! ENOUGH! 'A', It's not dinner time, and the sun's coming up shortly so half the crew will have to go below deck and we need enough _living_ slaves to stay on course, and 'B', We are running suspiciously short of humans lately. In fact, we seem to be short another _three_ of them tonight according to my first mate." Captain Damon Black nodded over to his best friend and first mate, Enzo Longjohn.

The British vampire began to speak. "That's right. Yesterday, we were down to ten remaining humans. Tonight, only seven reported to deck for work. The ratio of pirates to humans has become far below satisfactory. No one is allowed to kill humans without permission of either the captain or I, especially when the supply has dwindled so low. The last thing we need is to dessicate from starvation at sea before we have raided a civilian vessel for new assets. Henceforth, the punishment for killing any human shall be five rounds of keelhauling and being locked up below in vervained manacles until the next shore leave." Enzo concluded the announcement to the sound of some of the ship's vampire pirates grumbling in dissapointment, primarily the newest ones such as Mad Malakai, Logan Scumfell, and Billyboy Forbes. Thankfully, most of the older vampires had been on board for centuries and understood the value of living human captives, aside from Ripclaw and Kol who were longtime pains in the ass.

The Captain ignored the whining and nodded at his First Mate, then he returned his attention to his furious little brother, who's remaining right hand was visciously grasping the head of the injured human by his hair. Ripclaw was clearly struggling not to tear into the man's throat and rip his head off just to piss off Damon, but he knew that his big brother would have to make an example out of him and he'd get no mercy. Damon glared down at the incorrigible vampire until Stefan released the human, throwing him to the ground and turning his back on the Captain while stomping below deck.

"Saltz!" Damon called to his bosun.

"Aye Cap'n?" Alaric waited for his orders.

"Retrieve Ripclaw's daylight ring and bring it to me. He won't be setting foot above deck in daylight or on land for the next month. I will not tolerate disrespect!" Damon's jaw was clenched in anger. No other vampire on board would dare to behave in such a way, but they all knew Captain Damon Black's greatest weakness was his inability to kill his baby brother.

Damon was sick of Stefan's antics, the last thing he needed was a mutiny caused by a bloodlust riot. In general, the past century and a half had been very prosperous ever since Damon had taken the role of captain from his late father. The volatile Captain Giuseppe had been a brutal and hated pirate, and the crew had rejoiced when Damon led the 1864 mutiny against him. Most of the current vampires had been part of the revolt and had fought alongside the brothers against their father. Back then the two had been inseperable.

"Aye, aye, Cap'n." Ol' Saltydog nodded and gestured for Mason Lockbeard to follow him and assist in the ring's retrieval. Stefan would no doubt put up a fight.

If not for his ripper tendancies and frequent lack of control, Stefan would have likely been the first mate, but it would never happen as a result of too many instances of turning ripper and killing half the humans that the pirates could have enslaved during raids. Not to mention the disastrous incident of Stefan getting caught sleeping with his brother's former favorite concubine Katherine, which nearly resulted in Stefan walking the plank.

Instead, Damon had opted to save face by dueling his own brother in front of the crew, which ended in Stefan losing his left hand and begging for his life. The brothers had never fully been able to repair their relationship after the Katherine mess. In fact, sparing his brother meant another life had to pay. Katherine had regrettably been marooned on a desert island, and both brothers blamed each other for her loss. Stefan's humanity had become a thing of the past ever since.

Once Ric and Mason followed after Stefan, Damon ordered one of his pirate vampires to heal the injured human so he could return to work. After that, Enzo gave the order for all vampires without daylight rings to go below deck for the day. The Captain and First Mate then left to discuss plans for their next big raid. They were in desperate need of a large haul of supplies and humans, as their crew of vampire pirates had a very greedy appetite. Plus, raiding helpless coastal towns was always so much fun, but in modern times it required excessive planning. Alaric and another longtime trusted loyal vampire, the Second Mate Saint Niklaus joined them shortly after.

The four of them had been friends and allies for centuries, and along with Stefan and Nik's younger brother Kol they had been together all through the Golden Ages in the late 1600's and in the mutiny against Guiseppe. They all had daylight rings, which were an invaluable necessity at sea. Kol was a bit of a wild child, and though he had a ring he was not usually invited to the meetings due to his friendship with Stefan. Both of the younger brothers were ...difficult.

The only remaining former ally of Damon and Stefan's tyrannical overthrown father was ol' Mikey Mikaelson. He had been Giuseppe's first mate and had been spared because his expertise had been invaluable, but him and Saint Nik were longtime rivals, and Damon would never trust Mikey to be part of his inner circle. Nik and Kol's eldest brother, Elijah, had died in the fight against Giuseppe, and even though Mikey hadn't been the one to kill him, he was a reminder of their loss and the hatred remained. Nevertheless, he had a ring and was a skilled and powerful vampire pirate, and had remained aboard long after the mutiny.

The other pirates on board; Mason, Kai, Logan, and Billy, were all much less than a century old and had to stay below deck during the day. Damon was considering getting a daylight ring made for Mason because he'd been proving himself to be consistantly reliable for a few decades now, but getting any witch to help vampire pirates was extremely difficult. The other three were a different story. Modern newby vampires just weren't born from the same stock as the old crew, and they tended not to make quality pirates more often than not. Of course, over the long centuries they'd lost some of their best, and many others had gotten tired of life at sea eventually and gone back to being landlubbers.

Occassionally they'd get a veteran rejoining after decades on land got boring, but mostly they went through new recruits on a yearly basis. Logan would likely be one of those that failed, and Damon was still on the fence about keeping the psychopath Kai on board. There was also something about Billyboy that made the old crew a bit uncomfortable, but he didn't really know the guy very well. He'd need to send a few of his old friends to land to find some better recruits at some point, and maybe spend more time with them, but right now they needed to focus on satisfying the crew that they currently had. That meant that they needed to set up a raid for humans, booze, and women.

* * *

"This party's a hoot!" Matt shouted, throwing his hands in the air before grabbing his girlfriend Rebekah around her waist and spinning them around in circles a few times.

"You're wasted man!" laughed Tyler, as him and Caroline ran past them, holding hands.

Following a few yards behind them, best friends Elena and Bonnie chatted about all of their plans for next year at college. The six teenagers were all enjoying the night following their graduation ceremony earlier that day. Tyler's dad had even let him throw a massive class party at a beach house he owned, and noone remained sober.

"Dude, Ty, is that your boat?" Matt asked, pointed at a 30 foot long party boat tied up at the end of the dock at the beach house.

"Uhh, well its my dad's for when he wants to show off and take important people out, but I'm not really supposed to..."

"Oh, comon Tylerrrr, pleeease, please, please, I'll make it worth it," Caroline urged her boyfriend, sliding her hands up his chest seductively.

"Yeah Ty, come on, let's take it for a spin!" Matt joined in.

"Aaaah shit, I'm so gonna get my ass kicked!" Tyler whined as he caved to the pressure, and ran into the house for a moment, grabbed the boat keys, and ran back out jingling them with a big smile.

"Wheeeeeeeeeee!" shouted Rebekah in glee, and the four of them ran down the dock to the boat in excitement.

Bonnie and Elena looked at each other in shock for a second. Were their friends really going to 'steal' the mayor's party boat? Immediately they took off giggling and running after their friends; no way were they getting left behind!

Tyler had ridden on the boat with his father a few times and had a pretty good idea on how to get it going, so after a little trial and error, they were heading out from the Virginia coast towards the sea. Not long after getting the boat going, Tyler put Matt on the wheel so he could go below and get Caroline to make good on her promise. The other girls got drowsy after their long day and fell asleep on the boat's comfy seats. Rebekah started getting flirty and distracted her boyfriend from his duty at the wheel and soon they snuck off to a more private spot. Not a single person was at the wheel or even paying attention to where they were going or what was ahead of them.

As Tyler was thrusting into his girlfriend, he thought he felt the boat turning but he was too drunk and in ecstacy to stop. Once he felt Caroline squeeze around him and shout his name, he couldn't hold it in any more and seconds later he released. He rolled over onto his back beside her as the two of them panted, trying to catch their breath.

Right as Caroline was about to compliment him on a job well done, they heard what sounded like a snore, or snort, or both, coming from a small nook off to the side of the small cabin's mattress.

"What the...!?" Tyler shot up in bed and peered over the side. "Gilbert? Vicki? What the fuck are you two doing on my boat?"

Jeremy and Vicki were stuck in what looked like an impossible space, and they were both totally out of it.

"Oh, My. GOD!" Caroline yelled as she started dressing, running back up out of the cabin, shouting for Elena.

Moments later, Tyler, Matt, Rebekah, Caroline, Bonnie, and Elena were all down below attemping to pull the two unconcious druggies out of the crevice between the boat and the mattress, and the two had still yet to awaken.

"Unbelievable, what is he even doing at this party, he's not even a senior!" Elena was almost as furious as Tyler.

"Yeah, well at least he's still a kid, my sister just turned twenty and she's still working on getting a GED. She shouldn't be here either! What the hell did they take that knocked them out like this?" Matt was more embarrassed and shocked than he was angry. He was too worn down by the actions of his family to really get mad at his sister anymore. He was mostly worried about the fact that they were stuck in a tight spot and afraid she might suffocate.

As the chatty group of sleepy teenager's below deck pondered how they could wake up or retrieve the unconcious pair, they failed to notice the sounds above them.

That is, until they heard thumps on the steep staircase behind them, and a creepy voice calling out, "Well, well, well, what do we have here?"

The girls spun around screaming, Matt looked up saying "Huh?", and Tyler whipped around furiously, yelling, "NOW WHAT?"

Regardless of their initial reactions, the six of them were all terrified seconds later when the mysterious stranger looking down with an evil grin suddenly jumped down at them, his face morphing into a fanged monster.

Right behind him, more of the frightening inhuman intruders flew in through the small entrance, biting into their victims aggressively, and the cabin was full of screams, shrieks, and horrible laughter.

* * *

"Line them up so we can get a good look at them," Ric ordered, as the crew dragged their six pale and wimpering victims onto the _Salvatore_. Even as drained, exhausted, and frightened as they were, the four girls were _hot_. One of the boys looked like an able bodied lad, but mentally defeated. He'd be well suited as a ship slave. The other kid was still struggling and cursing, despite the hopelessness of his situation.

Enzo tilted his head amused. "That one's got some anger management issue's," he said chuckling as Damon walked over, nodding in agreement.

The other pirates had set the party boat to be towed behind them; it would fetch a nice price when they reached shore at their next destination. Suddenly, the captain narrowed his eyes as he spotted a thin woman stumbling up to the deck of the party boat that was being towed behind the ship.

"Hey, how the hell did you miss that one?" He yelled towards the youngest crew members, and the rest of the crew looked back at the unattended party boat in surprised.

"Shit." Logan Scumfell bowed his head in embarrassment, he'd been the last one off the boat and had declared it all clear.

The First Mate rolled his eyes and shook his head unimpressed, "Well, what are you standing there for? Go get her..." Enzo said to the fool.

"Aye, Cap'n" Scumfell answered nervously, climbing and jumping back to the party boat.

"What an idiot." Stefan taunted, and Kol laughed along with him.

Damon sighed. Had that moron just called Enzo the captain? One thing was for sure. "Worst vampire ever...who the hell recruited that guy anyway?"

"Billy, ahem" said Kai with a fake cough under his breath.

Everyone looked at Billyboy Forbes, who shrugged, replying "I thought he was cute at the time."

Some of the pirates groaned and others snickered. Damon looked over at Ric in annoyance.

"Saltz, since when are we allowing newbie vampires to recruit new crew?"

Alaric looked a little surprised himself. "Kol told me he recruited them."

The captain looked up at Kol, who had a colossal smirk. "Really, Kol? Was Scumfell yours or Billy's recruit?"

Kol laughed sheepishly. "It's called delegation, mate." Stefan bent over laughing and slapped his thigh. Nik's face turned red and he looked like he wanted to pummel his little brother.

"So then, who the hell recruited Billy?" now Damon was getting pissed off. The fact that Kol had addressed him as 'mate' instead of 'Captain' wasn't helping the matter at all.

"Kai did. Maybe he should tell the story." Billy was looking a little nervous.

"Don't mind if I do!" Mad Malakai spoke up happily, not waiting for the captain to respond. Ric face palmed, Enzo groaned, and Damon just raised his eyebrows and gestured for Kai to continue.

"This oughtta be good," Stefan sung out.

"So, here's the thing. I had just been turned a few weeks earlier, and after joyfully murdering most of my siblings, I was busy hunting down my youngest brother Luke. When I found him, he was hiding out shacked up with Billyboy's cheating ex boyfriend Steve, was it Steve or Stan? So I figured, why not have some fun? So, I had a chat with Billy, and told him if he wanted to get away with killing his ex-boyfriend, I'd turn him into a vampire. So I did, and it was the most hysterical homicide I've ever seen. Billy was soooo emotional when he turned, and wow! The blood and slaughter and crying was just a riot, I wish I had recorded it. So after he killed his ex, Stu, and my wittlest baby brudder Lukey, I thought, this guy would make a hilarious pirate!"

All of the old vampire pirates just stood there looking at Kai, completely stunned, including Kol and Stefan.

Mason was the first to recover, bursting out laughing, "Oh my God, what the hell man?" He went silent when he saw how irate the older vampires looked.

Damon took a deep breath. "Do I even want to know how we ended up with this nutcase on my ship?"

Kol raised his hand, looking a bit more nervous than amused at this point. "Uh, I ran into Kai at a pub, was a bit drunk, yeah? He had quite a list of murders under his belt already so I figured he'd fit right in. After that, like I said, I did some delegating. He said he'd get me some more badass recruits, and I told him to go at it. Then we got Billyboy. Then Scumfell. Do you want me to kill them?"

Damon looked over at Saint Niklaus, "If you don't get your brother and his managerie of dumbasses out of my sight..."

"Aye, mate, er Captain," Nik cringed and walked over to Kol who tried to run, but his big brother was a bit older and faster and managed to punch Kol in the face a handful of times before breaking his finger and pulling off the daylight ring. Kol stumbled back, glaring at Nik.

"Get below, little brother, and no more of this nonsense or it's shackles for you. Take your rejects with you while we figure this mess out. You will not recruit any more pirates ever again unless told otherwise."

Stefan, still laughing at his friend's predicament, slapped Kol on the back as the berated vampire angrily left.

It was at this moment, unfortunately for Logan Scumfell, that the youngest vampire finally returned to the ship while soaking wet, carrying a kicking Vicki Donovan over his shoulder and dragging a young teen boy by the leg behind him.

"So, I guess that there were actually two of them still over there," Logan said, looking around as all of the vampires turned their attention to him. Jeremy finally began to come out of his drug coma and kicked the vampire holding his leg, causing Logan to stumble forward and drop Vicki, who sat up and looked around confused.

"What?" Logan was starting to feel a little weirded out by the way the older vampires were staring at him, and he was completely shocked when the Captain walked towards him and ripped out his heart, tossing it overboard.

Right as the body landed, Stefan decided to pipe up, saying "Scum fell."


	2. Welcome Aboard

Welcome Aboard (The newcomer's first night):

* * *

Aside from a few wimpering humans kneeling side by side, the deck of the _Salvatore_ was eerily quiet for the first time all night. After the unexpected and shocking execution of one of his own pirates, Captain Damon Black had walked past the humans and vampires, pointing at Bonnie, simply telling Enzo to send her to his cabin and to deal with the rest however. Then he walked away.

Enzo, Ric, and Nik looked at each other. Tonight had been bizarre, but the Captain's response was beyond surprising. Unlike the late Captain Giuseppe di Salvatore, Damon had never killed a fellow pirate for such an insignificant reason.

The bosun was the first vampire back in action because he was most used to the necessity of giving orders rapidly when needed. "Lockbeard, toss that over the side," he pointed at Logan's dessicated corpse and Mason walked over to take care of it.

"Mikey, put that one to work," Ric pointed towards the quiet blonde human male, who stood up as the older vampire walked over, cursing the fact he'd been assigned to slave watch duty tonight. The gray haired pirate silently glared at the human before biting his own wrist and force feeding Matt a couple seconds worth of blood to get him back into working order. Then he roughly led Matt away from his human friends and sister and over to the other exhausted human ship slaves on board the _Salvatore_ , instructing them all to get back to work and supervising. Usually the humans had the night off to sleep and recover, but the pirates had returned them to work upon spotting the party boat. Mikey noticed that a few more seemed to be missing but he didn't feel like dealing with it.

"Any ideas on that one?" Alaric pointed at Tyler, who was still struggling defiantly against the ropes that had been necessary to bring the angry boy on board.

"Fuck you!" Tyler spat out.

"Not my type, kid." Ric said flatly, still looking at Enzo.

"Give him to Billy," Stefan joked while walking over to get a better look at the human girls since he'd been standing on the other side facing their backs. He gasped after getting a good look at Elena.

"Holy shit, she could practically be Katherine's clone." He wondered why his brother had ignored her. The girl's resemblance was uncanny. They weren't actually identical, but he'd be shocked if they weren't at least related directly, despite Katherine's marooning decades ago. "I'm taking this one, got a problem with that? Take it up with my brother."

"Ripclaw!" Enzo warned, but the vampire was already dragging the crying girl below deck as she kept calling out, "Jeremy!"

"Dammit, Stefan," muttered Alaric. Damon's asshole brother had no respect for the ship's designated heirarchy ever since turning off his humanity. His two 'on or off' personalities were complete opposites.

Saint Niklaus kept finding his eyes drawn to one of the blonde girls. After the bullshit with Kol, the elder brother wanted a pleasant distraction. He walked over and lifted the sniffling girl to her feet.

Suddenly, the angry human boy next to her went wild. "Don't you dare touch her!" he yelled as he stood up with his hands still tied behind his back and rushed at Niklaus attempting to shoulder check him. Nik released the girl momentarily and tossed to boy to the ground easily while laughing.

The kid tried to get back up shouting, "Caroline run!" which was pointless, as Niklaus just kicked him back down and held onto the blonde girl's arm, grinning at the little human that had tried to charge at him.

"Huh," chuckled Enzo. "Crazy little fellow, but at least he could still be useful now that we know what makes him tick. Those two are all yours Nik. See if you can break him so we don't have to just kill or compel him outright."

"That's exactly what I was thinking," Saint Niklaus replied smirking, allowing Tyler to finally stand up. He laughed as the boy stared daggers at him. "Alright mate, if you'd like this pretty little vixen to still be breathing tomorrow, you're going to do whatever I tell you, starting now. Walk." Niklaus pushed the kid forward, who for the first time was somewhat cooperative as he looked back worriedly at his girlfriend in the vampire's grasp.

After the three of them left, Ric ordered Mason to escort Bonnie to the Captain's cabin, and then to take over for Mikey with the working ship slaves until he had to go below deck for sunrise in a few hours. Mason nodded at the bosun, tugging the short, frightened dark skinned girl along as he left.

Ric and Enzo looked at the remaining three humans. Another beautiful blonde, and the two drenched stragglers that were still very confused and wasted.

"I fancy the blonde if you don't mind dealing with the others," Enzo spoke up quickly, his eyes on Rebekah. He was drawn to the way she seemed to be trying so hard to hold her nose up in a dignified manner, as if she was too important to be treated as a slave despite being captured by pirates. He was curious to find out how she'd react to the next few days.

"Awww, you bastard. Fine." Alaric grumbled, wanting more bourbon. His two humans were going to be useless until they were detoxed and could be actually be assessed. In their current state they both appeared to be dimwits. That didn't really matter to him; the boy could still work if he was a dimwit, and the young woman wasn't bad looking if she'd ever stopped glancing around in a stupor with a slack jaw.

The two pirates took their respective human charges and brought them below deck since they'd only have a few hours before it'd be sunrise and they'd need to return to work. They were going to be incredibly short staffed in the morning from the looks of things, and the rest of the human ship slaves were going to need a break before they started falling overboard.

* * *

The strong vampire known as Mason Lockbeard led Bonnie away from the people she knew and down into the dark interior of the ship to a closed door, before rapping on it a few times.

"Send her in," the voice she recognized as the dark haired Captain's called out. She found herself sinking to the floor where she stood in terror. This man, or whatever horrible monster he was, had chosen her after ripping out his own subordinate's heart right in front of everyone.

"Oh, come on," Mason mumbled as he found himself having to hold up the dead weight of the hyperventilating girl who was having some sort of panic attack.

Bonnie cried out startled as the door opened, and the blue eyed demon stood directly in front of her, watching her with interest.

"I'll take it from here." he said, sending Mason away and walking the girl into his cabin before shutting the door.

Wiping the tears off of her face, he gazed into her eyes to compel her, "Don't be afraid, we're just gonna start off with a little chat, mmkay?"

Bonnie narrowed her eyes, still feeling terrified, but managing to say back with a bit of anger, "How could I not be afraid after seeing what you did and what kind of monsters you are?!" She ripped her arms away from him, backing up after feeling his grip loosen.

Damon stared at the girl in surprise. Not only had her heartrate failed to slow down, but her lips still quivered in fear despite her firey little outburst.

"You're still afraid of me," he commented curiously with a slight smirk. "Are you a witch?"

"Excuse me?" The girl was completely baffled by his question.

"Interesting." Either she was something else entirely, or she was likely unaware that she was a witch. There were no signs of vervain, and his pirates had already drank blood from all of the newcomers before bringing them on board so she wasn't ingesting it. He pointed towards a chair, "Please, take a seat, miss?"

"Um, Bonnie," she said, very confused by how he was acting. She had expected a ruthless monster to rape her, and his odd question had her completely bewildered. She sat down, hoping that he would continue to just talk to her as long as she cooperated with harmless commands. She was emotionally and physically exhausted, and the wound on her neck from being bit by that crazy vampire Kai during the party boat attack was throbbing in pain.

"I'm Damon, welcome to the _Salvatore_ , 'Um Bonnie'," he grinned. He was having fun just watching all the different emotions on her face, particularly when she went from confused, to angry, and back to confused. Then she suddenly broke down and began to cry and he decided that it wasn't so much fun.

"Hey, no, don't cry. Stop. I'm not going to hurt you okay little Bon Bon?" He found himself sympathetically pleading with her before he realized what he was doing. This was not how he'd planned for this little meeting to go. Despite being a plundering vampire pirate captain who had killed thousands in his long 'life', he was never the kind of guy to force a woman to sleep with him. He preferred to simply compel away their fear and then get to know them a bit and flirt until they were seduced enough to temporarily forget he was a monster.

Sure, most of them were probably thinking that they'd be stupid _not_ to sleep with the pirate ship's captain, and on the rare occasion that they actually ended up rejecting his advances, he'd let them leave his cabin knowing that they'd just end up at the mercy of a less civil member of his crew. Ultimately, however, he found no pleasure in forcing an unwilling woman to sleep with him, so if his skilled experience in seducing a woman failed then he didn't want her.

That didn't mean he was a good man by any stretch of the imagination. He knew that realistically the humans that came aboard this pirate ship wouldn't leave untouched. If they chose to please him, they would have a much more pleasant journey until he grew tired of them and released them at some random port after compelling them to forget everything. He actually did enjoy getting to know them and wasn't going to just hand one of his girls off to get roughed up by other pirates even after he lost interest. Most of the other older pirates had a similar outlook, but there were definitely a few really sick bastards on board as well and he did nothing to stop them as long as they behaved the rest of the ship's rules.

No, there was nothing good about his intentions with the captured women no matter how kind and gentle he treated them in his own cabin or the fact that he preferred to befriend and eventually release them when things went well. The cold truth was that they'd been kidnapped and he used them, and if they chose not to be used by him, he let them leave his cabin only to suffer a worse fate at the hands of another pirate. He was as heartless of a womanizer as the rest of the vampires on the ship, and his kindness was always born from selfish desires. After all, he was a pirate.

The fact that he found himself begging this girl not to cry and genuinely wanted her to feel better, momentarily forgetting all about his self serving motivations, was a major slip up. After Katherine's shocking betrayal, he swore that he'd never allow himself to truly love or care for another woman ever again. He built a wall up and it had remained in him for decades now, so why on earth was this insignificant little woman actually affecting him? He knew that he should send her away if her tears were truly bothering him, but he didn't want to. He didn't want to let her get hurt. _Shit_. This had to stop.

"This masterpiece of a ship was built in 1649 for my grandfather, who named it after himself, but died before ever getting the chance to captain her." he said, hoping to distract her.

It seemed to work as she returned to her previous state of being confused, scoffing and blurting out, "What? How is that even possible, shouldn't it be an ancient relic at the bottom of the sea by now?"

He smiled, "Repairs, restorative renovations, many modern upgrades that are hidden under her authentic appearance..."

"So, you're trying to tell me that you've all been playing pirates on this giant sailboat for over 350 years? Do you even realize how impractical that is?" Bonnie couldn't even fathom how the modern day Navy hadn't sunk these lunatics.

"Who's playing?" Damon raised an eyebrow and smirked as she rolled her eyes.

"Why?" she asked, with a judgemental huff.

" _Why_? Because...why not?" Damon had answered that same question many times with much more snarky responses, but usually it was in response to a helpess human crying out something like _'why are you doing this to me?'_. This tiny little woman was actually talking to him as if he was some kind of ostentatious jackass instead of a ruthless centuries old master of the high seas. He could almost understand why after the ridiculous nonsense that had occurred on deck earlier due to the incompetance of a few newbies. Maybe he really was losing his touch as a notorious pirate captain if it was that easy for a few imbeciles to infiltrate his crew and allow this helpless woman to have him actually questioning the validity of it all.

Suddenly there was a knock on his door, and without standing up, he grinned and called to the human standing outside to come in. The door opened and a human woman brought over a dish, removing the lid and exposing a plate containing a mound of creamy yellow rice. "Risotto with saffron, as you ordered, Captain, and a glass of fresh water," the middle aged woman stated while setting it on the small table next to Bonnie.

"Thank you, Liz," he replied. "You may now go and rest for the night. If any of my men try to give you any grief, remind them that I don't tolerate anyone fucking with my friends." The blonde woman smiled at him and left appreciatively, closing the door behind her. It had been years since he'd slept with her and she'd become the cook for the ship's human population (after he'd given her his in-depth tutelage of traditional Italian recipes), but he had remained very fond of the aging woman. He'd never been in love with her, but her wellfare was important to him even decades after she had been captured and brought aboard.

Damon was pleased at the way this little scene seemed to stump Bonnie out of her judgey little attitude, and he invited her to eat the meal that had been brought up for her. She looked at it with suspicion so he rolled his eyes and began talking to her again.

"I've been a pirate for my entire life. It's what I was born and raised to be, and I've never had any regrets, so why wouldn't I want to continue living the most rewarding life in the world?" he said, thinking _'Why am I explaining myself to this girl that I should be ravishing or giving the boot by now?'_

"You've never wanted to do anything better with your life after hundreds of years?" Bonnie looked at him perplexed and still not touching the food, and he became irritated.

"Do tell me 'Um, Bonnie', what else should a 365 year old _vampire pirate Captain_ do, if he were to suddenly be having a mid-life crisis that prompted a desire for career change?" Damon said, developing a dangerous glint in his eyes that pulled Bonnie back to the reality of her situation.

She crossed her arms in an attempt to keep a grasp on the fear that wanted to bubble back up from the butterflies she felt in her stomach.

"Well, aside from kidnapping and killing innocent people, do you enjoy anything meaningful?" she asked, trying to keep a brave face. He narrowed his striking blue eyes at her and studied her in silence for a moment.

Suddenly he burst out laughing at her, as if he'd just been playing along with her questioning the whole time for his own amusement, which was partially true. She huffed again and and shook her head, making him laugh even harder at her as he stood up, towering over her. "You know what, little Bon Bon, I'm gonna give you some extra time to adjust to the way things work on a real life pirate ship. In fact, you can be my little tagalong later today and if you're nice, maybe I'll even give you a full tour. I highly suggest that you eat your dinner and get some rest right now, and when I return for you in a few hours you leave your judgey little remarks behind. If you can't agree to these terms, then feel free to leave my cabin while I'm on deck, but if you do, it's doubtful that you'll be even remotely safe." Damon turned and walked out, heading back up to take control of his ship. Hopefully the girl would be smart and still be there when he returned for her, as none of his pirates would dare invade his cabin to take her.

* * *

"Please, do whatever you want to me but don't let them hurt Jeremy!" Ripclaw frowned at this strange Katherine lookalike. She was turning out to be _nothing_ like the fun, sexy, rambunctious woman that he was hoping to pretend she'd be. She was _definitely_ not fun. She wouldn't stop whining about some 'Jeremy' that he couldn't care less about helping, and she kept trying to sacrifice herself to him if only he'd protect her poor, innocent, stupid little 'Jeremy'.

At one point he'd thought he'd made progress, as he had gotten her to cry out when he'd ripped off her sundress. Then she'd just gone limp and stopped fighting before he even did anything. This girl was so absurdly selfless in her attempts to just let him take her, with the hope that he'd save the 'Jeremy', that he couldn't even enjoy her one little bit. As boring as she was, there was no way he'd simply let her go. The guys would give him shit if he tried to trade her or even sent her away. How could she seriously be this much of a disappointment when she looked so much like Katherine? His mind kept straying back to his ex, threatening to trigger his emotions.

He missed Katherine far more than he missed his own left hand, and since 1953 he had spent all of his time doing whatever he could to cause all the trouble for his brother that he could get away with. She'd been his true love for nearly 89 years behind Damon's back, and half the reason he stayed on the ship was the hope that some day he'd find out where she'd been marooned and be able to rescue her. Despite the fact that she had been Damon's true love as a human, she had only been with Stefan's brother for a year before being tragically killed during the mutiny he'd helped Damon execute against their father in 1864.

Apparently, Damon had given her drops of his blood every day, and when she returned to life as a vampire, her affections had changed to favor Stefan over the newly elected Captain Damon Black. Of course, Damon had been too arrogant and blinded by his love for her to notice that for almost a century she spent all of her time with Stefan while he was too busy running the ship. Katherine had been the best part of Stefan's life before he'd lost her and became known as Ripclaw, and now he just wanted to get some satisfaction out of this new toy that looked almost just like her.

Everytime he decided to just take her whether she wanted to fight back or not, he found himself completely turned off at her total lack of survival instinct. She didn't even try, which made her practically the most opposite of his beloved Katherine as possible. He'd never been so frustrated and bored with a woman before in his life. If it wasn't for that fact that his brother would definitely follow through with all of the threats made in regards to killing humans without permission, he'd just rip her damn head off.

That was the other problem. His jerk of a big brother _knew_ that Ripclaw couldn't feed straight from humans without almost always killing them, so now he'd have to forego drinking directly from a vein and bleed his new girl's wrist into a damn cup in limited amounts at a time so he could stay in control enough to heal her and take more. His new toy was nothing but an epic tease, and he wasn't having any fun at all.

* * *

Elsewhere, First Mate Enzo Longjohn was having far better luck with his girl. Rebekah had been quite scared at first, but after being assured that he'd neither kill her or the others, she'd become rather pleasant company. She'd wanted to know if Matt would be okay, and seemed satisfied that he'd be fine as long as he did his work. The girl wasn't in love with the human boy and admitted that he was more of a high school crush, but she was still concerned for his wellfare. She'd only just moved to the town that the teens lived in and hadn't known them all more than several months before graduation.

Once Rebekah felt like she was being well treated and had nothing to worry about, she seemed to quickly relax and became quite flirty as he shared his wine with her. Enzo knew he had chosen the right girl from the lot; she responded rather delightfully to the affection and attention he willingly gave her and by the end of the night he was sure that they'd actually become friends. Without any compelling on his part, her ability to adjust to the predicament that she was in and overlook the horrors was absolutely remarkable, and she proved to be incredibly durable in bed as well. She came over a dozen times, and currently lay exhausted in his arms wearing nothing but the jewels he'd freely given her. It became clear to Enzo early on during their unbridled love making that this one was a keeper, he'd just have to spoil her rotten and keep the bad elements on the ship away from her.

The first part would be easy, the pirate life had led to an abundance in pretty treasures she clearly enjoyed being adorned with. The second part would be far trickier, after all, she was on a ship full of vampire pirates. Enzo just wanted to stay in bed all day, but he knew that he had to get back on deck before daylight. He'd have to make it very clear to the others that he'd claimed her as his, and that was partly why he left her covered in his bite marks in places that would remain visible when she wore clothes. As he stood and dressed himself, he left her a note to stay put in his room so she'd remain untouched, and that he'd have breakfast delivered to her when the cook awakened.

* * *

Kol Slawter, Mad Malakai, and Billyboy Forbes had been deeply engaged in their game of blood poker, having intercepted a few ship slave humans that had been on their way to bed, when Saint Niklaus passed them on his way down with Tyler and Caroline.

"Kol, send that human to bed and come with me, I've got a job for you to do, mate." Nik called out to his younger brother before telling the other two pirates that they better end their game before weakening the humans whose blood they were gambling with.

"Why not, this one's blood tastes like fish anyway," Kol said as he shoved the human he'd been abusing away from the table before standing up and following his brother. "What are we gonna do with them?"

Tyler glared at Kol with hatred, causing the vampire to grin mischievously as they reached the room that the sadistic brothers had been allowed to set aside for torturing trouble makers. While Niklaus normally showed a far more civil persona on deck, and had no problem following the Captain's rules, he was actually the cruelest of them all when humans or traitorous vampires ended up in this room. Kol, on the other hand, was consistantly barbaric, and never ceased walking the line of what was allowed, but even he rarely reached the levels that Saint Nik was willing to go to.

"This boy needs to learn his place. He made the foolish error of attempting to assault me earlier and still seems to believe that this girl belongs to him. You are going to show him how wrong he is. For now, no permanent maiming will be required, but all healable injuries of any sort shall be permitted. Keep him in one piece, and once you've broken him down some, I'll be back to check on your progress," Saint Niklaus spoke, watching as Tyler fought against Kol who had untied the kid only to chain him to the wall, unrolling a cloth filled with horrifying instruments.

"Oh my God! Please, don't hurt him!" Caroline squealed in protest.

"Shhh, love. You'll see him again soon, I promise. Once Kol gets him warmed up, we'll be back to join in on the next step. With any luck, he'll be ready to join the other ship slaves in a few days." Nik whispered softly into the blonde's ear.

"Wait, don't I get to play with her too?" Kol pouted as Nik had begun to lead her away.

"This girl will not be touched by you. She's mine. I have other plans for her," he replied, and this resulted in Tyler roaring and shouting endless vulgarities, spitting at Kol as the pirate approached him with a sharp object.

"Big mistake, _Darling,_ " was the last thing Caroline heard Kol say to Tyler as Niklaus closed the thick wooden door behind them on their way out, leading her to an upper level of the ship. On their way past the break room where Kai and Billy were still playing blood poker, they passed ol' Saltydog leading the two human charges he'd finally managed to get to their feet.

"I'm going to be busy for a while Alaric," said Niklaus to the bosun, who nodded on his way over to the poker table.

"The Captain's on deck already, passed him on the way down so he should be able to run things without us for a bit." Ric said, plunking Vicki and Jeremy at the card table. "I've gotta get these two dimwits bled sober, then I'll probably head up too."

Nik chuckled as he watched Ric grab a bottle of bourbon before turning away again and leading Caroline up to his little studio. As second mate, his room was quite small but still seperate from the rest of the crew. Caroline let out a gasp as she entered, looking around in shock at the walls. He locked his door and led her over to his bed, gesturing for her to take a seat and relax.

"Now, princess, you finally see my true intent," He said with a happy grin. Pointing to a bowl full of fruit and bottle of wine next to his bedside he added, "please help yourself while I get started." Caroline didn't know what else to do, but temporarily relieved she grabbed an apple and poured herself some wine to settle her nerves. Then she watched as the pirate picked up a blank piece of canvas and put it on his easel, beginning to paint.

She took another look at the walls around his room, noting that while all the paintings were of different women, some of them appeared in modern clothing while other's were dressed in outfits resembling the 17th, 18th, and 19th centuries. Being very tired as well as distracted by the paintings and the way that the strange pirate gazed attentively at her while he painted, she forgot about the fact that Tyler was currently having a very different experience and took another bite out of her apple.

* * *

A few minutes into the game of blood poker, Alaric decided that the two humans that had been 'playing' the game before his own arrival were looking overly famished and pale, so he sent them away to get sleep. Now it was just him, Kai, Billy, and two very dazed and confused human teenagers. Seeing as how they were short a human, he removed himself from the game, instructing Kai and Billy to get the two humans in working shape. Under no circumstances were the human's to end up dead, or they'd likely be joining Scumfell's fate based on the Captain's current temperament. He finished his bourbon and headed back up, certain that the two young vampires weren't suicidal and would do as they'd been told.

Not long after Ric left, Vicki was showing signs of being far more aware of her surroundings, and it wasn't long before she was starting to get fidgety and wanted to start doing gymnastics in the break room. It reminded her of the Mystic Falls Grill, containing a bar stocked primarily with bourbon, and various pub games such as a pool table and dartboard. Kai decided that it would be fun to dance around with her, so he activated the juke box and the two of them began having a grand old time. He figured that she probably thought she was at some random party, and saw no reason to tell her otherwise, as long as he was enjoying himself. It wasn't long before he had the silly girl twirling around and blood sharing with him, she just couldn't seem to get enough.

With Kai and Vicki doing their own thing in the break room, a very confused Jeremy found himself in the care of Billy. They were walking down some weird hallway and he had no idea where he was, but the dude that was guiding him had a very strong grip around his shoulder. Jeremy figured the guy was probably kicking him out of some party, and he was trying to locate his phone in his pockets to call for a ride home. For some reason his clothes were soaked, so he wondered if he'd fallen in a pool but couldn't really remember. He couldn't find his phone and decided that it must be dead anyway.

"Heyyy uhh could maybee use your phone?" The boy tried to say but the guy didn't answer, continuing to lead Jeremy through the halls and down a wooden stairway into what appeared to be a storage room.

"Whhas the hell's goin on man?" Jeremy babbled as he toppled over into a crate when the man let him go and turned around to go shut the doorway.

Before Billy managed to shut the door, shouting came from down the hall, "JEREMY?!"

Jeremy's ears perked up at the familiar voice as he was struggling to stand back up, and before Billy had sped over to cover his mouth he'd managed to shout a reply, "Elena?!"

Seconds later, the heavy door that Billy hadn't fully shut burst open, with a very bored looking Ripclaw standing there with Elena. She wept for joy and ran over to her little brother, hugging him in relief. Stefan rolled his eyes, walking past a very annoyed Billy and pulled Elena back away from her brother.

"See, the 'Jeremy' is alive and kicking, time for you to start putting out." Ripclaw said, interrupting their reunion.

"Elena, where are we? What's going on?" Jeremy asked, becoming very concerned.

"Don't worry, I'll take good care of the kid for ya sweetie, " Billy said, trying to get her to shut up so Ripclaw would take her and go away. The girl didn't miss the way he seemed so interested in her baby brother, and her fighting instincts finally kicked into full gear.

"No!" Elena shouted, smacking Stefan in the face, her palm missing his cheek and hitting his nose full force, before managing to twist off his left hook that she'd noticed had become a bit loose, spinning around and stabbing Billy in the eye with it before he'd even realized what had happened since he was too busy paying attention to Jeremy.

"Ow!" yelled Stefan, holding his broken nose, before fixing the cartilage back into place with a twist and heading over to Billy to retrieve his left hook. The younger pirate was hysterically trying to remove the hook without hurting himself.

"Holy Shit, Elena!" yelled Jeremy as she took his hand and started running with him past the two pirates and out of the storage room. She pulled the heavy door behind her and slammed a board into place to keep it shut, taking her brother's hand again and beginning to run through the halls of the ship.

Stefan ignored the door shutting and yanked his hook out of Billy's orbital socket, yanking the eye out with it and the younger vampire fell down holding his hand to the hole in his face and screaming. Ripclaw screwed his hook back into place on his left stump tightly before flicking the eyeball at Billy and walking casually over to the door, kicking it open and snapping the board that had held it shut. _Now THIS is fun_ , he thought to himself as he began casually hunting down his fleeing toys.

* * *

Author's Note:

Just to be clear, the pirate Mikael in this AU story is not at all related to the pirate brothers Niklaus and Kol, and none of them are related to this human version of Rebekah. Also, The human Liz in this story was absolutely never ever married to Billy, and the human girl Caroline is not their daughter. Tyler and Mason are not related either. These character's are all AU versions with different lives than they had in the show.

One last thing so that there isn't any confusion, I decided that I'm not using the whole doppelganger thing in this story, so Katherine and Elena look 'very similar' but aren't clones.


End file.
